Several classes of non-cyclic acetylenic compounds have been isolated from terrestrial plants as well as from marine organisms. Most of these compounds fall into the basic category referred to as the polyacetylenic compounds, having more than one acetylenic moiety. Several groups have reported the isolation of these polyacetylenic compounds from marine organisms. The acetylenic carbinols identified to date from marine organisms have been shown to contain more than one acetylenic carbinol moieties. See the following publications:
Cimino, G., A. Crispino, S. De Rosa, S. De Stefano and G. Sodano (1981) "Polyacetylenes from the sponge Petrosia ficiformis found in dark caves," Experientia 37:924-926. PA1 Fusetani, N., Y. Kato, S. Matsunaga and K. Hashimoto (1983) "Bioactive marine metabolites III. A novel polyacetylene alcohol, inhibitor of cell division in fertilized sea urchin eggs, from the marine sponge Tetrosia sp.," Tetrahedron Letters, 24 (27):2771-2774. PA1 Wright, A. E., O. J. McConnell, S. Kohmoto, M. S. Lui, W. Thompson and K. M. Snader (1987) "Duryne, a new cytotoxic agent from the marine sponge Cribrochalina dura," Tetrahedron Letters, 28 (13):1377-1380. PA1 Castiello, D., G. Cimino, S. De Rosa, B. De Stefano and G. Sodano (1980) "High molecular weight polyacetylenes from the nudibranch Peltodoris atromaculata and the sponge Petrosia ficiformis," Tetrahedron Letters 21:5047-5050. PA1 Cimino, G., A. DeGiulio, S. De Rosa, S. De Stefano and G. Sodano (1985) "Further high molecular weight polyacetylenes from the sponge Petrosia ficiformis," J. Natural Products, Vol. 48, 1:22-27. PA1 Quinoa, E. and P. Crews (1988) "Melynes, polyacetylene constituents from a Vanuatu sponge," Tetrahedron Letters, 29 (17):2037-2040. PA1 Rotem, M. and Y. Kashman (1979) "New polyacetylenes from the sponge Siphonochalina sp.," Tetrahedron Letters 34:3193-3106. PA1 Fusetani, N., M. Sugano, S. Matsunaga and K. Hashimoto (1987) "H,KATPase inhibitors from the marine sponge Siphonochalina truncata: Absolute configuration of siphonodiol and two related metabolites," Tetrahedron Letters, 28 (37):4311-4312. PA1 Hansen, L. and P. M. Boll (1986) "Polyacetylenes in Araliaceae: Their chemistry, biosynthesis and biological significance," Phytochemistry, 25 (2):285-293. PA1 (1) The invention compounds are non-cyclic monoacetylenic carbinols; PA1 (2) The invention compounds are unique in having a single terminal 3-ol, 4-en, 1-yne moiety attached to an alkyl chain; and, PA1 (3) These invention compounds are the first report of such acetylenic compounds known to possess immunosuppressive activities.
The compounds of the subject invention are clearly different from the prior art as follows: